Alkamides natural

In 2004, Ley et al. [45] showed a stereoselective enzymatic synthesis of cis-pellitorine [N-isobutyldeca-(2 ,4Z)-dienamide], a taste-active alkamide naturally occurring in tarragon. The reactants were ethyl ( ,Z)-2,4-decadienoate— the pear ester described before—and isobutyl amine. The reaction is catalysed by lipase type B from Candida antarctica (commercially available), which shows a remarkable selectivity towards the 2 ,4Z ester. The yield was about 80%. 

Greger, H., Comparative phytochemistry of the alkamides, in Conference on Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC) (J. Lam, H. Breteler, T. Amason, and L. Hansen, eds.), 159-178, Elsevier, Amsterdam, 1988. 

Alkamides are also typical and relevant constituents of E. purpurea roots and aerial parts. They should be used for quality control besides the determination of cichoric acid. While absorbtion of alkamides can be suspected from their lipophilic nature and from the fact that they are responsible for the local anaesthetic effect ( tingling sensation ) on the tongue [28], bioavailability of cichoric acid still needs to be determined. Nevertheless, both compounds are good markers for a reproducible manufacturing process, because they readily undergo degradation when extraction and storage parameters are not optimal. 

Greger H (1988) Comparative Phytochemistry of the Alkamides. In J Lam, H Breteler, T. Arnason, L Hansen (eds) Chemistry and biology of naturally-occurring acetylenes and related compounds. Elsevier, Amsterdam, 159-178... 

Natural and Synthetic Alkamides Applications in Pain Therapy... 

All theories of the natural origin of these alkamide series should be studied in more detail. There is a lack of information on the chemical, enzymatic, and genetic aspects on the biosynthesis that should be studied. 

Decades of investigations in the natural products chemistry of the Piper genus yielded an important amount of monomeric and dimeric alkamides of diverse molecular architectures crnitributing to their biological activities [20-23,203,208-219]. Specifically, [4+2] dimers were isolated in P. chaba while [2 + 2] dimers were isolated in P. nigrum and P. longum, in both cases together with monomeric amides. 

Piperine is the major constituent found within the fruits of P. nigrum, P. longum, and many other Piper species. This natural alkamide is responsible for the taste and smell of pepper. It is estimated that each person in the United States consumes a daily intake of 21 mg of piperine [223]. Biologically, this... 

Today, more than 300 alkamides have been isolated as natural products and more than 100 of their synthetic analogs have been prepared. A large variety of biological activities have been described for these compounds. However, three activities are predominantly important analgesic attributed to the alkenylamides isolated from some Asteraceae, Capsicum and Piper species immunomodulatory associated to the characteristic W-alkynylamides found in some of the Asteraceae plants and antifungal and insecticidal shown for the sulfurated alkamides from Glycosmis. 

Chem. Descrip. 1 1 Oieamide DEA Ionic Nature Nonionic CAS 93-83-4 EiNECS/ELiNCS 202-281-7 Uses Thickener, superfatting agent, emulsifier for lotion shampoos Properties Liq. 100% act. 85% amide Alkamide DS-280 [Rhodia Novecare]... 

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